Wishing for a Do-Over: Overcoming Regret to Create a New Career Story

A few days ago I found an old anonymous post online. Its writer pleaded for advice and help. He told a common story.

At the time of writing, he was 41 years old, toiling away at a menial job he hated, making just above minimum wage. In his case at a nursing home - many of which are short staffed, with absurd patient-carer ratios and zero lunch breaks.

Basically, he reported, he had nothing going for him. No money, no savings, no skills, no career capital, no friends, no life experiences. 

He felt like he wasted his 20s and 30s. He wished he had traveled, went to concerts, or at least built a career. He felt like he wasted his chance to make high-achieving friends and network connections.

Finally, he shared his worries that he was too late to “catch up to” everyone else. Along with two piercing questions.

“Is it too late? Am I too old to start over?”

These fears aren’t limited to people over 40. Many people in their 30s, or even mid 20s, grapple with similar fears. Even some recent university graduates start regretting their education specialty.

The post was too old for me to reply, but here’s what I’d tell him—and anyone else harboring the same doubts.

Is it too late to start over? The short answer is

No.

The long answer is

No, but it may not be easy. You can start over at 31, 41, 51, or even 61. But the sooner you begin, the better.

A few suggestions for anyone in the same situation

Many people responded with some great advice:

1. Forget about everyone else: Whatever “they” say or do doesn’t matter. Just focus on what’s best for you and Future You. Define your own picture of success, which you don’t need to limit to mountains of money or prestige. 

2. Go to the library: Check out 5 autobiographies or biographies about people who found success later in life.

Look for people like Julia Child (published her first cookbook at 50 years old), Stan Lee (published the Fantastic Four at 40 years old), or Vera Wang (entered the fashion world at 40 years old).

Their journeys will likely spark a few ideas. At the very least, they might inspire you or boost your confidence. Especially if anything you read resonates directly with your experience.

3. Imagine you have a best friend: If he was in your situation, what would you tell him? Figure out the direction you want to go. Reflect on the lessons life has been trying to teach you all these years.

Write it all down.

4. Pick 3 things you can do today: No matter how small. The little steps you take now will add up into bigger things. Then tomorrow pick 3 more. And the next day, and the next day, and the next day, one day at a time. The important thing is to always keep moving.

5. Meet people: Don’t worry about deliberate professional networking yet. There are many free or cheap hobby groups and events. One day, perhaps, you’ll start your own. Lack of skills or experience doesn’t kill dreams. Isolation does. 

Ultimately, the world needs more compassion. Including self-compassion. Past You did the best he could, with the limited information he had at the time.

If you can relate to the anonymous writer, please go through these suggestions

I know you can do it. And, if someone you know is in a similar position and these suggestions could help, please share this. It’s important they know they’re not alone.

You’ve got this.